Ammonium formate → HCID 68737789, compound

HRID 529159Notes

Reaction equation

HRID 529159 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][N:23]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:15]([C:36]3[C:37]4[CH:44]([CH:45]([CH3:47])[CH3:46])[CH2:43][CH2:42][C:38]=4[N:39]=[CH:40][N:41]=3)[CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:31]1([N:23]([CH2:22][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[N:15]([C:36]4[C:37]5[CH:44]([CH:45]([CH3:47])[CH3:46])[CH2:43][CH2:42][C:38]=5[N:39]=[CH:40][N:41]=4)[CH2:14][C:11]4([CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:21]=23)[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86651818HCID 86651818, compound

Product 1

HCID 68737789HCID 68737789, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl(cyclopentyl)carbamate (0.095 g, 0.15 mmol) in MeOH (1 mL) was treated with Pd/C (0.0079 g, 0.0075 mmol) and ammonium formate (0.028 g, 0.45 mmol) and heated to reflux for 7 hours then stirred at room temperature overnight. The reaction was filtered through glass filter paper, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (5% MeOH/DCM then 5% 7N NH4 in MeOH/DCM) to yield tert-butyl cyclopentyl((1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)carbamate (0.066 g, 81%). LCMS (APCI+) m/z 546.1 [M+H]+; Rt=4.25 min.

Workup

  1. temperatureheated
  2. temperatureto reflux for 7 hours
  3. filtrationThe reaction was filtered through glass
  4. filtrationfilter paper
  5. customthe solvent was removed under reduced pressure
  6. customThe crude residue was purified by column chromatography (5% MeOH/DCM

Sources & evidence

ORD record
ord-8ae20e5732ca478191fd31f2d9fe03b1
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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